ES2404336T3 - Procedimientos para la preparación de compuestos de aminosulfona - Google Patents

Procedimientos para la preparación de compuestos de aminosulfona Download PDF

Info

Publication number: ES2404336T3
Authority: ES; Spain
Prior art keywords: formula; acid; process according; reaction; solvent
Prior art date: 2008-09-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES09789280T

Other languages

English (en)

Spanish (es)

Inventor

Manohar T. Saindane

Chuansheng Ge

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Celgene Corp

Original Assignee

Celgene Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-09-10

Filing date

2009-09-09

Publication date

2013-05-27

2009-09-09 Application filed by Celgene Corp filed Critical Celgene Corp

2013-05-27 Application granted granted Critical

2013-05-27 Publication of ES2404336T3 publication Critical patent/ES2404336T3/es

Status Active legal-status Critical Current

2029-09-09 Anticipated expiration legal-status Critical

Links

238000000034 method Methods 0.000 title claims description 50
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 title description 8
238000002360 preparation method Methods 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 28
150000003839 salts Chemical class 0.000 claims abstract description 28
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
150000002081 enamines Chemical class 0.000 claims abstract description 11
239000012453 solvate Substances 0.000 claims abstract description 10
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 9
150000002825 nitriles Chemical class 0.000 claims abstract description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 56
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
238000006243 chemical reaction Methods 0.000 claims description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 34
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 32
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 27
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
239000002904 solvent Substances 0.000 claims description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
230000008569 process Effects 0.000 claims description 19
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
230000009467 reduction Effects 0.000 claims description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
239000012279 sodium borohydride Substances 0.000 claims description 9
229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
230000007062 hydrolysis Effects 0.000 claims description 8
238000006460 hydrolysis reaction Methods 0.000 claims description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
SWKPKONEIZGROQ-UHFFFAOYSA-N 4-trifluoromethylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(F)(F)F)C=C1 SWKPKONEIZGROQ-UHFFFAOYSA-N 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 4
229940098779 methanesulfonic acid Drugs 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
239000002841 Lewis acid Substances 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims 3
238000004519 manufacturing process Methods 0.000 abstract description 6
-1 aminosulfone compound Chemical class 0.000 description 38
239000000203 mixture Substances 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 19
239000000126 substance Substances 0.000 description 16
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 14
XTIINWPNAMHVDG-UHFFFAOYSA-N 3-ethoxy-4-methoxybenzonitrile Chemical compound CCOC1=CC(C#N)=CC=C1OC XTIINWPNAMHVDG-UHFFFAOYSA-N 0.000 description 12
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 11
230000035484 reaction time Effects 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 9
229940049920 malate Drugs 0.000 description 8
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 8
108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
239000008367 deionised water Substances 0.000 description 5
229910021641 deionized water Inorganic materials 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
VAMZHXWLGRQSJS-UHFFFAOYSA-N 3-ethoxy-4-methoxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC=C1OC VAMZHXWLGRQSJS-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
102100040247 Tumor necrosis factor Human genes 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000010992 reflux Methods 0.000 description 4
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 3
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
IMOZEMNVLZVGJZ-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 IMOZEMNVLZVGJZ-UHFFFAOYSA-N 0.000 description 3
239000000376 reactant Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
229910003074 TiCl4 Inorganic materials 0.000 description 2
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
230000001363 autoimmune Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 2
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 1
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ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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229950008913 edisilate Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
229960001731 gluceptate Drugs 0.000 description 1
KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229940049906 glutamate Drugs 0.000 description 1
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000000592 heterocycloalkyl group Chemical group 0.000 description 1
125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 1
125000004476 heterocycloamino group Chemical group 0.000 description 1
125000004470 heterocyclooxy group Chemical group 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
238000011835 investigation Methods 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
229940099584 lactobionate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
ZBODFFYYETUYLG-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dihydroisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2CC3=C(NC(C)=O)C=CC=C3C2)=C1 ZBODFFYYETUYLG-UHFFFAOYSA-N 0.000 description 1
229950006327 napsilate Drugs 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229940014662 pantothenate Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229950002757 teoclate Drugs 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ES09789280T 2008-09-10 2009-09-09 Procedimientos para la preparación de compuestos de aminosulfona Active ES2404336T3 (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US9590208P	2008-09-10	2008-09-10
US95902P		2008-09-10
PCT/US2009/005055 WO2010030345A2 (fr)	2008-09-10	2009-09-09	Procédés pour la préparation de composés d’aminosulfone

Publications (1)

Publication Number	Publication Date
ES2404336T3 true ES2404336T3 (es)	2013-05-27

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ID=41565187

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Application Number	Title	Priority Date	Filing Date
ES09789280T Active ES2404336T3 (es)	2008-09-10	2009-09-09	Procedimientos para la preparación de compuestos de aminosulfona

Country Status (15)

Country	Link
US (1)	US8242310B2 (fr)
EP (1)	EP2334639B1 (fr)
JP (1)	JP5513508B2 (fr)
CN (1)	CN102209709B (fr)
CA (1)	CA2736171A1 (fr)
DK (1)	DK2334639T3 (fr)
ES (1)	ES2404336T3 (fr)
HR (1)	HRP20130356T1 (fr)
MX (1)	MX2011002589A (fr)
MY (1)	MY155424A (fr)
PL (1)	PL2334639T3 (fr)
PT (1)	PT2334639E (fr)
SI (1)	SI2334639T1 (fr)
SM (1)	SMT201300045B (fr)
WO (1)	WO2010030345A2 (fr)

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US9126906B2 (en) *	2012-02-21	2015-09-08	Celgene Corporation	Asymmetric synthetic processes for the preparation of aminosulfone compounds
EP2764866A1 (fr)	2013-02-07	2014-08-13	IP Gesellschaft für Management mbH	Inhibiteurs de l'enzyme activant nedd8
WO2014151180A1 (fr)	2013-03-14	2014-09-25	Celgene Corporation	Traitement de la polyarthrite psoriasique à l'aide d'apremilast
EP3539539B1 (fr)	2013-06-17	2025-11-05	Amgen (Europe) GmbH	Formulations de comprimés de (+)-2-[1+3-ethoxy-4-méthoxyphényl)-(-2-méthylsulfonyléthyl]-4-acétylaminoisoindoline-1,3-dione
ES2751773T3 (es)	2014-05-15	2020-04-01	Amgen Europe Gmbh	Uso de inhibidores pde4 y combinaciones de los mismos para el tratamiento de la fibrosis quística
WO2015175956A1 (fr)	2014-05-16	2015-11-19	Celgene Corporation	Compositions et procédés de traitement de maladies cardiovasculaires athérosclérotiques à l'aide de modulateurs de pde4
EP2949645A1 (fr)	2014-05-28	2015-12-02	LEK Pharmaceuticals d.d.	Procédés de préparation de composés ß-aminosulfone
MX2016014384A (es)	2014-06-23	2017-01-20	Celgene Corp	Apremilast para el tratamiento de una enfermedad del higado o una anormalidad en la funcion del higado.
US10092541B2 (en)	2014-08-15	2018-10-09	Celgene Corporation	Methods for the treatment of diseases ameliorated by PDE4 inhibition using dosage titration of apremilast
JP2018516912A (ja) *	2015-05-26	2018-06-28	ルピン・リミテッド	アプレミラストおよびその新規な多形の改善された製造方法
EP3307711A1 (fr) *	2015-06-09	2018-04-18	Dr. Reddy's Laboratories Ltd.	Procédé de préparation de l'aprémilast et de ses intermédiaires
EP3106457A1 (fr)	2015-06-15	2016-12-21	LEK Pharmaceuticals d.d.	Nouvelle voie synthetique vers l'apremilast
EP3144393A1 (fr)	2015-09-18	2017-03-22	LEK Pharmaceuticals d.d.	Voie synthétique vers l'apremilast
EP3356327A1 (fr)	2015-09-29	2018-08-08	Pliva Hrvatska D.O.O.	Procédés de préparation d'aprémilast, et ses intermédiaires
WO2017070291A1 (fr)	2015-10-21	2017-04-27	Celgene Corporation	Modulateurs de pde4 pour le traitement et la prévention du syndrome inflammatoire de reconstitution immunitaire (iris)
EP3373916A1 (fr)	2015-11-11	2018-09-19	Celgene Corporation	Formes pharmaceutiques orales à libération contrôlée de médicaments faiblement solubles et leurs utilisations
US10774041B2 (en)	2016-04-15	2020-09-15	Davuluri Ramamohan Rao	Process for the preparation of apremilast
CN106543050B (zh) *	2016-09-28	2018-04-10	中南大学湘雅医院	一种阿普斯特中间体的合成工艺
EP3606907B1 (fr)	2017-04-04	2021-01-20	Quimica Sintetica, S.A.	Composés de bêta-aminosulfone racémiques
SI3606908T1 (sl)	2017-04-04	2020-10-30	Quimica Sintetica, S.A.	Delitev racemičnih beta-aminosulfonskih spojin
CN107011209A (zh) *	2017-05-11	2017-08-04	蚌埠中实化学技术有限公司	一种3‑甲氧基‑4‑乙氧基苯腈的合成新工艺
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2009
- 2009-09-09 EP EP09789280A patent/EP2334639B1/fr active Active
- 2009-09-09 HR HRP20130356AT patent/HRP20130356T1/hr unknown
- 2009-09-09 WO PCT/US2009/005055 patent/WO2010030345A2/fr not_active Ceased
- 2009-09-09 JP JP2011526855A patent/JP5513508B2/ja active Active
- 2009-09-09 PL PL09789280T patent/PL2334639T3/pl unknown
- 2009-09-09 ES ES09789280T patent/ES2404336T3/es active Active
- 2009-09-09 MX MX2011002589A patent/MX2011002589A/es active IP Right Grant
- 2009-09-09 SI SI200930584T patent/SI2334639T1/sl unknown
- 2009-09-09 CN CN200980144555.0A patent/CN102209709B/zh active Active
- 2009-09-09 DK DK09789280.6T patent/DK2334639T3/da active
- 2009-09-09 US US12/556,479 patent/US8242310B2/en active Active
- 2009-09-09 PT PT97892806T patent/PT2334639E/pt unknown
- 2009-09-09 MY MYPI2011001053A patent/MY155424A/en unknown
- 2009-09-09 CA CA2736171A patent/CA2736171A1/fr not_active Abandoned
2013
- 2013-04-19 SM SM201300045T patent/SMT201300045B/xx unknown

Also Published As

Publication number	Publication date
JP5513508B2 (ja)	2014-06-04
MX2011002589A (es)	2011-04-07
US20100168475A1 (en)	2010-07-01
EP2334639B1 (fr)	2013-01-23
HRP20130356T1 (en)	2013-05-31
SI2334639T1 (sl)	2013-06-28
CN102209709A (zh)	2011-10-05
CN102209709B (zh)	2014-08-13
PT2334639E (pt)	2013-04-26
PL2334639T3 (pl)	2013-08-30
MY155424A (en)	2015-10-15
WO2010030345A2 (fr)	2010-03-18
US8242310B2 (en)	2012-08-14
HK1159064A1 (en)	2012-07-27
CA2736171A1 (fr)	2010-03-18
DK2334639T3 (da)	2013-05-06
JP2012502097A (ja)	2012-01-26
SMT201300045B (it)	2013-07-09
WO2010030345A3 (fr)	2010-05-06
EP2334639A2 (fr)	2011-06-22

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